5-benzylidene-9-n-butyl-2,3,5,6,7,8-hexahydro-4(1H)-acridinone | 135105-78-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-benzylidene-9-n-butyl-2,3,5,6,7,8-hexahydro-4(1H)-acridinone
• 英文别名: 5-benzylidene-9-butyl-2,3,5,6,7,8-hexahydroacridin-4(1H)-one；(5E)-5-benzylidene-9-butyl-1,2,3,6,7,8-hexahydroacridin-4-one
• CAS: 135105-78-1
• 化学式: C₂₄H₂₇NO
• 分子量: 345.484
• InChiKey: ZJLRELFNKUJYGZ-FBMGVBCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-benzylidene-9-n-butyl-2,3,5,6,7,8-hexahydro-4(1H)-acridinone 在 ammonium hydroxide 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 28.5h， 生成 2-Amino-7-butyl-11-oxo-5,6,8,9,10,11-hexahydro-benzo[b][1,10]phenanthroline-3-carbonitrile
  参考文献：
  名称：

  Bell, Thomas W.; Hou, Zheng; Zimmerman, Steven C., Angewandte Chemie, 1995, vol. 107, # 19, p. 2321 - 2324

  摘要：

  DOI：
• 作为产物：
  描述：

  5-benzylidene-9-butyl-1,2,3,4,5,6,7,8-octahydroacridin-4-ol 在 乙酸酐 、 二甲基亚砜 作用下， 反应 16.0h， 以71%的产率得到5-benzylidene-9-n-butyl-2,3,5,6,7,8-hexahydro-4(1H)-acridinone
  参考文献：
  名称：

  Molecular Architecture. 2.¹ Synthesis and Metal Complexation of Heptacyclic Terpyridyl Molecular Clefts

  摘要：

  Methods are described for the synthesis of a series of functionalized derivatives of 9-butyl-1,2,3,4,5,6,7,8-octahydroacridine (9), a building block for several types of highly preorganized host compounds. A key intermediate is 5-benzylidene-9-butyl-2,3,5,6,7,8-hexahydroacridin-4(1H)-one (23), which can also be used in the syntheses of torands and hydrogen-bonding hexagonal lattice receptors. A tridentate cleft (20), consisting of 2,2';6',2 "-terpyridine imbedded in a heptacyclic framework, and a corresponding pentadentate diketone (6) were synthesized from 9 in five and seven steps, respectively. The picrate extraction method was used to estimate the solution stabilities of alkali metal complexes of heptacyclic terpyridyls 6 and 20, which was also compared with a flexible terpyridyl (37). Alkali metal complexes of both heptacyclic terpyridyls showed relatively high K-s values, but low size selectivity. Pentadentate host 6 binds Na+ and K+ more strongly than do most hexadentate crown ethers; flexible tridentate analogue 37 failed to extract alkali metal picrates into chloroform. The complexation abilities of 6 and 20 are attributed to enforced orientation of functional group dipoles toward the center of the molecular cleft. Sodium and potassium picrate complexes of pentadentate cleft 6 were synthesized (1:1 stoichiometry), and a 2:1 complex of calcium triflate (6(2) . Ca(CF3SO3)(2)) was also prepared.

  DOI：

  10.1021/jo9720041

文献信息

• Expanded heterohelicenes: molecular coils that form chiral complexes
  作者：Thomas W. Bell、Helene Jousselin

  DOI：10.1021/ja00016a062

  日期：1991.7
• Torands: rigid toroidal macrocycles. Calcium sequestration by a member of this new ligand class
  作者：Thomas W. Bell、Albert. Firestone

  DOI：10.1021/ja00285a049

  日期：1986.12
• BELL, THOMAS W.;LIU, JIA, ANGEW. CHEM., 102,(1990) N, C. 931-933
  作者：BELL, THOMAS W.、LIU, JIA

  DOI：——

  日期：——
• BELL, THOMAS W.;LIU, JIA, J. AMER. CHEM. SOC., 110,(1988) N 11, 3673-3674
  作者：BELL, THOMAS W.、LIU, JIA

  DOI：——

  日期：——
• BELL T. W.; FIRESTONE A., J. AMER. CHEM. SOC., 108,(1986) N 25, 8109-8111
  作者：BELL T. W.、 FIRESTONE A.

  DOI：——

  日期：——